The Pitfalls of Matchmaking
by HolaitsCiara
Summary: AU: "I need you to teach me how to seduce a woman."- Leo Valdez thought he knew what he was getting himself into when he agreed to wingman for Nico di Angelo. Thanks to Piper McLean, he couldn't have been more wrong.
1. Part One: The Beginning

The plan had been brilliant.

The execution: flawless.

Leo Valdez's plan to get Nico di Angelo a girlfriend had been an obvious success from the start. That was until Piper McLean came along.

* * *

It is a universal truth that good friends wingman for one another. Leo Valdez is no stranger to that, having been a wingman—and a damn good one at that—many times for Frank, Jake, and sometimes even Jason—yes, the man, the _legend_, has had his issues when communicating with the opposite sex (read: Piper McLean). However, experiences aside, never once in his life as a wingman did he ever think that the young, awkward, socially-inept, and seemingly-asexual Nico di Angelo would ever need, let alone _want, _his help.

Then again, he has been wrong before.

* * *

**PART ONE: THE BEGINNING**

It was Friday night, and Leo had yet again, dragged them (Nico, Jason, Percy, and Frank) into some new club he'd recently heard about. The five of them sat in a booth, drinks in hand (aside from Nico who had a giant red stamp labelled 'underage' on his hand, which ultimately ruined his chances with any alcoholic beverage), leaning closely to the centre of the table as Leo began to tell them a joke.

Leo was just about to say the punchline when Nico blurted something out, thus silencing everyone: "I need you to teach me how to seduce a woman."

Leo blinked, thinking maybe he'd heard the other boy wrong. Maybe he'd had too much to drink already. After all, since when did Nico express interest in _anyone? _Leo looked up at his surroundings. _If the room started spinning, then I _definitely _heard Nico wrong_, he thought as his eyes roamed around the club, which—for lack of a better term—was packed.

The dance floor was chock-full of drunk bodies grinding against each other as some indie band played onstage, thinking they're the second coming of The Strokes. Snobby hipsters littered the back, each one staking claim on the title of who heard said band before anyone else.

No spinning, he noted.

Leo turned his head. On another side of the room sat the bar, absolutely packed with possibly-future-alcoholics, alcoholics in general, and the most douchiest-looking group of guys Leo had ever seen. A smirk graced Leo's features when he saw one of them—the prepubescent Bruce Willis look-alike—try to convince the bartender that they were of drinking age.

Still no spinning.

Leo turned his head back, slowly facing the group. He was about to say something when he (1) closed his eyes and thought about it, (2) realized how much of an ass he'd sound so he closed his mouth again, and (3) opened his eyes, looked at Nico and just stared.

"I need you to teach me how to seduce a woman," Nico repeated in such a monotonous tone he could've easily passed for a robot.

Pause. "Um, Leo?"

Stare.

"Earth to Leo!"

Another pause.

Leo blinked several times. "Am I being Punk'd? Is Ashton here?"

* * *

**AN: I'd like to point out that I've been pretty much AWOL from FF for at least a year or so, and so I have no clue whether or not someone's already hatched this baby (story) up. If you could let me know, that'd be great. Thanks.**

**Anyway, I know this was short, but it's just an introduction, so let me know your thoughts! Also, if I've somehow piqued your interest with this, I warn you: updates will not come quick. But I won't pull a George R.R. Martin on you, I promise. :)**

**-Ciara**


	2. Leo Valdez Hated Mornings

Leo Valdez hated mornings.

It was Saturday morning; the sun was up, traffic was surprisingly not that bad (for the time being), and the sweet aroma emanating from the café across the street wafted through the windows of Leo's apartment building. Normally, such a day would have been considered absolutely glorious had Leo not been woken up by some inconsiderate asshole's incessant knocking.

Shutting his eyes, Leo covered the side of his head with a pillow and willed the knocking to stop. When the knocking finally ceased, Leo felt himself relax, succumbing to the comfort of his bed and allowing his dreams to consume him once more.

That's when the knocking started back up again.

Leo growled and threw the covers off. The moment his feet hit the cold, wooden floor, he realized he wouldn't be able to go back to sleep later on, which only served to irritate him further. With his senses livened up, he walked angrily to the front door, making his steps a lot heavier, and the string of profanities that left his mouth a lot louder than necessary. (Because he _had_ to let whoever was on the other side of the door know what kind of inconvenience they were being.)

Without bothering to check who said "inconvenience" was, Leo threw the door open and let the tirade begin. "What could you possibly want at this un_godly_ hour, that you need to knock so relentlessly on my front door—" he gestured animatedly to the aforementioned door "—which, by the way, is undoubtedly dented by now—"

He stopped abruptly and immediately began apologizing because standing before him were three of the scariest people he'd ever met: Hazel Levesque, Rachel Elizabeth Dare, and Annabeth Chase.

"Good Morning!" Rachel smiled brightly up at him, completely undeterred by his outburst. "We brought you some muffins!"

* * *

How would one begin to describe Annabeth Chase? For one, she's ridiculously smart, having been Mensa certified since she was fifteen years-old. For another, she's extremely terrifying! Unless, of course, you happen to be Percy Jackson because then she'd be a bumbling fool (in a totally Annabeth-esque sort of way).

"Leo," Annabeth said once she and her companions had settled themselves on Leo's couch. She looked pointedly at him as he moved restlessly around the room. "Calm down, we're just here to talk to you.

"Those never end well..." he mumbled, taking a tentative seat across from his guests.

"What?"

"Nothing."

Annabeth's grey eyes narrowed into slits, but she chose to let the subject go, much to Leo's relief. "Anyhow, we're here to help you."

That came as a surprise. Leo was sure that Annabeth had come to bite his head off for agreeing to Nico's request or for allowing Percy to get drunk—both of which wouldn't be a first for her. After all, Annabeth had developed a soft-spot for Nico over the years (she'll deny it, but it's true), with her weird sister-like antics having a tendency to come out whenever and wherever Nico was concerned. "With what?" Leo asked slowly.

"Setting Nico up with a girl," Hazel piped in.

Hazel Levesque is a lot of things. For one, she's one of Leo's favourite people in the world. With her wit, charm, and impeccable taste music—how could she not be? Fake ex-girlfriend is another title fit for her, but that's a whole other story.

"Oh, okay," Leo said, a hint of confusion lacing his tone, and then he added, "Wait, why do you want to help?"

Hazel looked confused. "Because he's my brother..."

Leo shook his head, perfectly aware of the strong bond between the two siblings. "No, I know that, but why are _you two_ so gung-ho about this?" he said, looking at Annabeth and Rachel.

"Look, I'm not saying I wholeheartedly approve of your quest to find Nico a girlfriend since he should be focusing on his studies instead. However, Nico is like a brother to me, and I want him to be happy," Annabeth said. "Plus, it'll help me sleep better at night knowing that Nico's future-girlfriend is someone who sees the value in education."

"A _girlfriend_?" Leo was at a loss for words. "I thought he just wanted to—"

Leo stopped abruptly upon receiving a glare from Annabeth. Quickly, he looked to Rachel for her explanation, eyebrows raised.

"I have nothing better to do with my day," Rachel said, shrugging.

That was a first.

Leo never quite understood Rachel, which in hindsight of their previous relationship, actually makes a lot of sense. Being the daughter of one of New York's wealthiest men, Rachel Elizabeth Dare could easily have it all. However, Rachel Elizabeth Dare has a lot of rules, like not taking money from her father. That particular one had always baffled Leo, who had grown up in a family that could barely make ends meet, especially when he took into account Rachel's less-than-desired living conditions.

Nonetheless, between attending school and working, Rachel never seems to have enough time on her hands, which was a primary factor to their falling-out, and the reason why Leo found it so difficult to comprehend the mere thought of Rachel "having nothing better to do". However, when Rachel didn't bother to provide any more details as to why she wanted to help, Leo simply clapped his hands together and said, "Okay, ladies, what's the plan?"

Wearing matching grins, the three women huddled around him and began formulating their plan. The only time they would pause was to reprimand Leo on whatever he was doing at the time, and by the end of it, Leo couldn't help but feel bitter towards the might-have-been of what would normally be a glorious Saturday.

When they finally finished with their planning (or as Leo liked to call "scheming"), Annabeth, Rachel, and Hazel all decided to head out. Leo was mid-jump (made from pure relief and happiness) when Hazel paused at the door and turned to face him.

"By the way, we're having a welcome back party for Piper tomorrow," Hazel smiled. "You should come!"

Leo froze. "Piper's back?" he squeaked.

"Yeah."

Leo started to nod when a thought suddenly dawned on him. "Does Jason know about this?"

A nervous laugh escaped Hazel's lips. "About that," she said, looking anywhere but his direction. "I was kind of hoping that—"

"I'd be the one to tell him?"

"Yeah," Hazel let out a deep breath, allowing Leo to process the situation. "Thanks Leo, bye!" she said with forced enthusiasm. Not taking the chance of having Leo flat-out reject the idea, she booked it.

Leo sighed. "Crap."

Yep, he hated mornings.

* * *

**an: a surprisingly quick update from me... hooray! author's notes are so much easier in list-form. so here you go: **

**-yes, this is a Piper/Leo story**

**-no, there will be no myths and other magical goodness, hence the AU**

**-there will be some bromance action in upcoming chapters!**

**-let me know what you think of this chapter, yeah? **

**bye for now,**

**Ciara**


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